3',4'-Dimethoxycinnamic acid → HCID 67343122, compound

HRID 1673541Notes

Reaction equation

HRID 1673541 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([OH:16])=O.[NH2:22][C:23]1[CH:35]=[C:34]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:13]/[C:14]([NH:22][C:23]2[CH:35]=[C:34]([CH2:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:16])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

7

Reactant 3

HCID 168483',4'-Dimethoxycinnamic acidHCID 65578Oxalyl chlorideHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67343122HCID 67343122, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.0 mL of Methylene chloride, 0.010 mL of N,N-dimethylformamide and 0.064 mL of oxalyl chloride were added to 0.13 g of 3,4-dimethoxycinnamic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 1.5 mL of methylene chloride and 0.14 mL of triethylamine containing 0.15 g or tert-butyl 2-amino-4-phenethylbenzoate while ice-cooled and stirred at room temperature overnight. The solvent was evaporated under reduced pressure and ethyl acetate and 10% critic acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed, with 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=4:1] to obtain 0.12 g of tert-butyl 2-((E)-3-(3,4-dimethoxyphenyl)acrylamido)-4-phenethylbenzoate as white solid.

Workup

  1. temperaturecooled
  2. stirringstirred at room temperature overnight
  3. customThe solvent was evaporated under reduced pressure and ethyl acetate and 10% critic acid aqueous solution
  4. additionwere added
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed, with 10% citric acid aqueous solution
  8. customa saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-d3b22c7238d741bb86e367e77364e2a8
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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